Deals on vacations and trips to Tarrytown

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Tarrytown flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $413, price is now $188 per person
$188
per person
Feb 28 - Mar 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This smoke-free resort features a water park, a marina, and 2 restaurants. There's fun for all ages with a children's club and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and get free self parking.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $1,141, price is now $291 per person
$291
per person
Feb 24 - Mar 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This hotel features an outdoor pool, a gym, and a restaurant. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.
The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Price was $880, price is now $307 per person
$307
per person
Feb 26 - Mar 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and an arcade/game room, and complimentary bicycles are available on site. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $1,573, price is now $692 per person
$692
per person
Mar 8 - Mar 11
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Free water park access and an outdoor pool are featured at this smoke-free condo resort. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. There's fun for all ages with a lazy river and a children's pool, and barbecue grills are available on site.
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Save 100% on your flight
Price was $874, price is now $407 per person
$407
per person
Feb 23 - Feb 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
This resort features a golf course, a full-service spa, and 3 restaurants. Bring the family and enjoy the children's pool, playground, and kid-friendly dining. Enjoy the 2 outdoor pools and perks like free WiFi.

Top Tarrytown hotels deals

Days Inn by Wyndham Brooksville/Dade City

Days Inn by Wyndham Brooksville/Dade City

2 out of 5
6320 Windmere Rd Brooksville FL
Free Cancellation
Reserve now, pay when you stay
$75 nightly
The price is $83 total per night
$83 total
Dec 25 - Dec 26
Total with taxes and fees
This motel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Pool
Breakfast included
Microtel Inn & Suites by Wyndham Brooksville

Microtel Inn & Suites by Wyndham Brooksville

2 out of 5
6298 Nature Coast Blvd Brooksville FL
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $94 total per night
$94 total
Dec 28 - Dec 29
Total with taxes and fees
This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like continental breakfast and free self parking.
Pool
Breakfast included
Microtel Inn & Suites by Wyndham Bushnell

Microtel Inn & Suites by Wyndham Bushnell

2 out of 5
2612 West County Road 48 Bushnell FL
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $81 total per night
$81 total
Dec 25 - Dec 26
Total with taxes and fees
This hotel features an outdoor pool and a rooftop terrace. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
Hampton Inn Brooksville Dade

Hampton Inn Brooksville Dade

2.5 out of 5
30301 Cortez Blvd Brooksville FL
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $123 total per night
$123 total
Dec 31 - Jan 1, 2026
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and onsite conference space. A gym and luggage storage are also provided.
Breakfast included
Pet friendly
Hampton Inn Dade City - Zephyrhills

Hampton Inn Dade City - Zephyrhills

2.5 out of 5
13215 Us Highway 301 Dade City FL
Free Cancellation
Reserve now, pay when you stay
$113 nightly
The price is $127 total per night
$127 total
Jan 22 - Jan 23, 2026
Total with taxes and fees
This hotel features an outdoor pool and a gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A business center, a snack bar/deli, and express check-out are also on offer.
Pool
Breakfast included
Holiday Inn Express Hotel & Suites Brooksville by IHG

Holiday Inn Express Hotel & Suites Brooksville by IHG

2.5 out of 5
30455 Cortez Blvd Brooksville FL
Free Cancellation
$107 nightly
The price is $119 total per night
$119 total
Dec 28 - Dec 29
Total with taxes and fees
This hotel features an outdoor pool and a gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A business center, a terrace, and a snack bar/deli are also on offer.
Pool
Breakfast included
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Webster Westside Flea Market

4/5(24 reviews)

You can do some window-shopping at Webster Westside Flea Market during your trip to Webster. You can enjoy the coffeehouses while in the area.

Webster Westside Flea Market

Frequently asked questions

How much are vacation packages to Tarrytown?
$188 is all you'll need for an amazing vacation in Tarrytown. Bundle your hotel and flights into a Travelocity vacation package and see the savings start to grow. With prices as good as these, it's never been easier to travel!
Where can I get the best vacation package deals for Tarrytown?
You can grab sensational Tarrytown package deals with Travelocity. Choose from as many as 400 partner airlines and 1,000,000 properties worldwide and turn those vacation dreams into a reality.
Why should I purchase my Tarrytown vacation package with Travelocity?
We offer round-the-clock support, exceptional service and a Price Match Guarantee. Life's a great big journey — and we have amazing destinations for you to journey to all across the world. Wander with us and your wallet will thank you for it.
Can I save on my Tarrytown car rental if I book it with my hotel or flight?
Definitely — and if you also add an activity or experience to your Tarrytown vacation package, you'll pick up even greater savings. With one of our affordable packages, you can find things to do around the region that are just right for you. Then, hop in your rental car and work your way through the list. Universal Studios Florida is one renowned attraction to check out. It's located 35 mi from Tarrytown.

Photos of local treasures

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